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一种高效、廉价且储存稳定的重氮转移试剂:盐酸咪唑-1-磺酰叠氮化物。

An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride.

作者信息

Goddard-Borger Ethan D, Stick Robert V

机构信息

Chemistry M313, School of Biomedical, Biomolecular & Chemical Sciences, The University of Western Australia, Crawley WA 6009, Australia.

出版信息

Org Lett. 2007 Sep 13;9(19):3797-800. doi: 10.1021/ol701581g. Epub 2007 Aug 22.

Abstract

The design and synthesis of a new diazotransfer reagent, imidazole-1-sulfonyl azide hydrochloride, are reported. This reagent has proven to equal triflyl azide in its ability to act as a "diazo donor" in the conversion of both primary amines into azides and activated methylene substrates into diazo compounds. Crucially, this reagent can be prepared in a one-pot reaction on a large scale from inexpensive materials, is shelf-stable, and is conveniently crystalline.

摘要

报道了一种新型重氮转移试剂——盐酸咪唑-1-磺酰叠氮的设计与合成。该试剂已被证明在将伯胺转化为叠氮化物以及将活性亚甲基底物转化为重氮化合物的过程中,作为“重氮供体”的能力与三氟甲磺酰叠氮相当。至关重要的是,这种试剂可以由廉价材料通过一锅法大规模制备,具有货架稳定性,并且易于结晶。

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